During my 40-plus years of integrating technology into business and education, the biggest obstacles were not faulty products or excessive costs, but the objections of people. Those same people were also the heroes of education technology because some had the vision to see the bigger picture and the potential implications of new tools before anyone else. Early in my career, I found those objections particularly grating because they were what separated me and my technology from the world of successful, completed projects. It took moving to an elite boarding school as IT director to reframe and refocus what I now consider truly important when we introduce technology to people: setting up the balance between data and dignity, the idea that we must consider people and their agency when responsibly implementing and using technology.